Synlett

The Synthesis of Chiral Polyhydroxylated Pyrrolidines Using a Reverse-Cope Cyclisation

IA O'Neil, E Cleator, N Hone, JM Southern…

Index: O'Neil, Ian A.; Cleator, Ed; Southern, J. Mike; Hone, Neal; Tapolczay, David J. Synlett, 2000 , # 5 p. 695 - 697

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Citation Number: 11

Abstract

Abstract: Ring opening of (2S, 3R)-1, 2-epoxy-4-penten-3-ol with N-benzylhydroxylamine hydrochloride and NaOMe in methanol gives the amine oxide (9) as a single diastereoisomer in 72% yield. Catalytic hydrogenation furnishes the parent homochiral pyrrolidine (10) in quantitative yield. Key words: pyrrolidines, asymmetric synthesis, cyclisation, hydroxylamine, reverse-Cope

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